Colin Cowherd Podcast - David Ross Talks 2016 Cubs Magic, Team USA Pressure & Launching New Podcast

Podcast: The Herd with Colin Cowherd
Date: March 25, 2026
Episode Theme: David Ross discusses the legacy of the 2016 Cubs World Series, launching “The Lovable Reunion” podcast with Anthony Rizzo, Team USA’s intensity in the World Baseball Classic, and reflections on modern baseball.

Episode Overview

Colin Cowherd sits down with former Cubs manager, 2016 Cubs catcher, and two-time World Series champion David Ross. The episode explores the lasting legacy of the 2016 Cubs championship, the behind-the-scenes camaraderie that made that team special, the high-stakes environment of Team USA at the World Baseball Classic, and the evolution of baseball’s personalities and economics. Ross also discusses launching "The Lovable Reunion" podcast with Anthony Rizzo, promising fans a nostalgic, in-depth journey through one of sports' most lovable championship runs.

Key Discussion Points & Insights

The Origin of “The Lovable Reunion” Podcast

[07:17] David Ross explains:

• The idea came up after Rizzo's retirement (~2 years ago), driven by their strong friendship and chemistry.
• “We’re so excited. This has been a journey that’s taken on a life of its own already with the guys.”
• They wanted to bring a fun, authentic voice to baseball podcasting, involving old teammates and candid stories.
• The group at The Volume was especially enthusiastic, which helped seal the deal.
• “It just was such a fit. … There was nobody more excited and kind of on board with whatever we wanted to do.” [08:03]

The Magic and Pressure of the 2016 Cubs

[09:05] Colin reflects on the national pressure:

• “The country, even outside of Chicago, the country was rooting for Chicago. … It was almost Olympic feeling.”

Ross on momentum & confidence:

• The team’s belief started in late 2015, with young talent and an influx of key veterans.
• “A lot of people, we really hit that momentum … in a series in San Francisco, 2015.” [10:34]
• Joe Maddon’s messaging: “Embrace the target was our slogan going into 16 and we took all. It was amazing.” [12:30]

Joe Maddon’s Leadership and Culture

[14:41] Ross discusses Joe Maddon:

• Joe’s eclectic, big-picture approach unified young and veteran players.
• Openly discussed his controversial decisions in the 2016 Series: “He spoke very eloquently about, you know, his plan … letting him walk you through some of his decision making.” [15:13]

The Unique Experience of Playing (and Winning) in Chicago

[17:43] Colin on Chicago’s vibe:

• "Chicago can be distracting. It's a drinking city, it's a food city... This is like Miami North."

[18:00] Ross on being a Cub in a party city:

• “First of all, everybody ... I want, you would think when I walk into a restaurant, I'm Michael Jordan and I'm the backup catcher.”
• "You're not going to win a World Series or championship with a bunch of choir boys. ... We definitely had our mix." [19:04]
• Emphasizes tight clubhouse bonds, late nights, and how Maddon created a bubble against external pressure.

Behind-the-Scenes: The Final Game & Game 7 Emotions

[26:01] Cowherd asks Ross to recall the dugout in Game 7:

• “It’s tense... all the anxiety, all the, you know, the tension that you hold, just the relief that you have of, you know, we did it.” [27:08]
• Nuanced details like Rizzo catching the final out and the rollercoaster of bullpen decisions.

Wrigleyville and Fan Expectations

[29:29] Ross on Wrigleyville:

• "They call it the biggest beer garden in Illinois."
• Contrasts Dodger fan base: “Wrigley’s young, Wrigley’s a party.” [29:32]

Baseball Personalities: Fitting in as a Cub

[30:37] Ross on player fit (re: Kyle Tucker):

• Emphasizes the challenge of being a quieter superstar in Chicago, a city that craves visible passion and leadership.
• “The guys that can stay a little more unemotional, I think it’s a really, really positive. ... They want somebody to either be pissed or... I wear my heart on my sleeve and I think it’s going to be great for this podcast.” [32:50]

World Baseball Classic: Intensity and Meaning

[34:41] On Team USA's experience:

• “It did feel like every one of them felt like playoff games. ... The expectations, even when facing Great Britain – we’re supposed to pound them.”
• Venezuela game intensity: “Pat McAfee told me after the game... that may be the best sporting event I’ve ever been to live.” [36:00]
• “I've never seen a group of men come together so fast... as that Team USA team was.” [36:34]

Baseball Economics and the Dodgers “Issue”

[37:23] Cowherd on market dynamics:

• Advocates for a spending floor, not a cap: most successful small market teams spend ~$130–160M.
• “Don’t force high income teams ... to play by St. Louis’s economy.”

[40:18] Ross on big spenders:

• “I think everybody would be okay with a floor without a ceiling. ... The Dodgers are good for baseball.”
• Highlights how Dodgers blend smart front-office strategy with financial muscle.
• “If you have a smart front office ... you can have a really good baseball team.”

2016 Cubs Legacy and Lasting Impact

[47:50] Ross on what the championship means:

• “Me personally, those guys and how they lifted me up in that. I mean, I got carried off the field Game 7. Who’s that happening to?”
• Explains how that moment elevated his career opportunities and personal legacy.
• “My life has taken off since that championship, and a lot of that has to do with... the staff and obviously the players. That city. It’s meant so much to me.” [48:39]

Emotional Player Interviews & Locker Room Bonds

[49:50] On the most emotional podcast interview:

• “Kyle Schwarber. This last one we just did. … He is so great. … Just how it changed their life.”
• Mike Montgomery also got emotional thinking about getting the last out.

The Grind of a Baseball Season & Clubhouse Brotherhood

[51:37] Ross shares a funny moment of in-house tension:

• Tells a story of Anthony Rizzo making a public comment on the pitching staff, John Lester’s reaction, and the kind of familial tough love that kept the clubhouse honest.

[53:14] On the unique family-like bond in baseball:

• “We start around Valentine’s Day … we didn’t get home till November. ... You’re with these guys every single day. … Your family within that clubhouse, you see those guys every single day and you’re working and pulling for them and their success is your success.”
• Emotional anecdotes including teammates flying Ross home for family emergencies.

Cubs Outlook, Milwaukee Rivalry, and Optimism for 2026

[55:46] On the Cubs this year:

• Praises new additions (Bregman, Kate Horton): “They’ve got some dudes up there in Chicago.”
• Thinks the Milwaukee rivalry will be fierce: “It should be a fun, fun season. Opening day is here upon us.” [56:31]

Notable Quotes & Memorable Moments

• “[Chicago] is like Miami North. There is a... it does not close down at 9:30. It is a live city.” – Colin Cowherd [16:18]
• “I want, you would think when I walk into a restaurant, I’m Michael Jordan and I’m the backup catcher.” – David Ross [18:00]
• “You’re not going to win a World Series or championship with a bunch of choir boys. ... We definitely had our mix.” – David Ross [19:04]
• “I think everybody would be okay with a floor without a ceiling. ... The Dodgers are good for baseball.” – David Ross [40:18]
• “My life has taken off since that championship, and a lot of that has to do with... the staff and obviously the players. That city. It’s meant so much to me.” – David Ross [48:39]
• “We start around Valentine’s Day … we didn’t get home till November. ... Your family within that clubhouse, you see those guys every single day and you’re working and pulling for them and their success is your success.” – David Ross [53:14]

Key Timestamps

• 07:17: Ross on launching “The Lovable Reunion” podcast
• 10:34: When the 2016 Cubs’ belief took off
• 14:41: Insights on Joe Maddon and managing the Cubs
• 18:00: Life and nightlife as a Cub in Chicago
• 26:01: Recalling the final outs of Game 7
• 29:29: Culture of Wrigleyville and Chicago fanbase
• 34:41: Team USA in the World Baseball Classic
• 40:18: Ross on Dodgers, baseball economics, and the need for a salary floor
• 47:50: The lasting personal meaning of the Cubs championship
• 49:50: Most emotional player interviews for the new podcast
• 51:37: In-house “tough love” and the grind of the season
• 53:14: The unique family bond of a baseball clubhouse
• 55:46: Cubs outlook for 2026 and the rise of the Milwaukee rivalry

Tone and Style

The episode is warm, reflective, and conversational, blending fond nostalgia with candid, humorous, and sometimes deeply personal insights. Ross is open about both the emotional and technical sides of baseball, the personalities that influenced the Cubs’ 2016 magic, and the real-life pressures of high-stakes events like the WBC. Cowherd mixes sharp analysis with playful banter, ensuring the discussion stays accessible and engaging for all listeners.

For New Listeners

This episode is essential listening for baseball fans, especially those interested in the human stories behind legendary teams. It offers a rich behind-the-scenes view of the 2016 Cubs, the evolution of team culture in modern baseball, how personalities shape locker rooms, and why the next decade remains bright for the game. Ross’ forthcoming “Lovable Reunion” podcast promises more of the same unfiltered, heartfelt storytelling.